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Updated: Jan 18, 2026

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
Reaching the Limit of Inverted Solvatochromism in π-Extended Bipyridinium-Phenolate Dyes
Fabián Melinao1, Matías Vidal1, Raúl Mera-Adasme2
1Facultad de Química y Biología, Universidad de Santiago de Chile, Av. Bernardo O'Higgins 3363, Santiago 9170022, Chile.
Abstract:
A series of π-extended bipyridinium-N-phenolate dyes were synthesized to examine the combined effects of π-extension and a second pyridinium unit on solvatochromism. The UV-vis spectral behavior of all dyes follows an inverted solvatochromic tendency, with absorptivity values depending on the viscosity of the media due to reduced planarity. TDDFT calculations reproduced the spectra and clarified the charge-transfer pathways, highlighting the critical role of planarity and conjugation in tuning solvatochromic responses.
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